NPASS Compound

Structure

NPC474360 OpenBabel07101718322D 30 32 0 0 1 0 0 0 0 0999 V2000 3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3660 -2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 -2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 7 1 0 0 0 0 2 22 1 0 0 0 0 3 22 1 0 0 0 0 4 23 1 0 0 0 0 5 29 1 0 0 0 0 6 30 1 0 0 0 0 7 8 1 0 0 0 0 8 12 1 0 0 0 0 9 11 2 0 0 0 0 9 13 1 0 0 0 0 10 11 1 0 0 0 0 10 14 2 0 0 0 0 11 15 1 0 0 0 0 12 15 1 0 0 0 0 12 16 2 0 0 0 0 13 17 2 0 0 0 0 13 22 1 0 0 0 0 14 16 1 0 0 0 0 14 29 1 0 0 0 0 15 18 2 0 0 0 0 16 20 1 0 0 0 0 17 18 1 0 0 0 0 17 19 1 0 0 0 0 18 24 1 0 0 0 0 19 23 1 0 0 0 0 19 25 2 0 0 0 0 20 26 2 0 0 0 0 20 30 1 0 0 0 0 21 22 1 0 0 0 0 21 23 1 0 0 0 0 21 27 2 0 0 0 0 23 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	414.17
Volume:	421.135
LogP:	4.08
LogD:	3.034
LogS:	-4.335
# Rotatable Bonds:	5
TPSA:	110.13
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.584
Synthetic Accessibility Score:	3.526
Fsp3:	0.435
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.936
MDCK Permeability:	1.4107446077105124e-05
Pgp-inhibitor:	0.799
Pgp-substrate:	0.317
Human Intestinal Absorption (HIA):	0.075
20% Bioavailability (F20%):	0.1
30% Bioavailability (F30%):	0.048

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.137
Plasma Protein Binding (PPB):	94.67594909667969%
Volume Distribution (VD):	0.948
Pgp-substrate:	3.752828359603882%

ADMET: Metabolism

CYP1A2-inhibitor:	0.692
CYP1A2-substrate:	0.964
CYP2C19-inhibitor:	0.754
CYP2C19-substrate:	0.883
CYP2C9-inhibitor:	0.67
CYP2C9-substrate:	0.728
CYP2D6-inhibitor:	0.392
CYP2D6-substrate:	0.154
CYP3A4-inhibitor:	0.654
CYP3A4-substrate:	0.902

ADMET: Excretion

Clearance (CL):	3.553
Half-life (T1/2):	0.379

ADMET: Toxicity

hERG Blockers:	0.006
Human Hepatotoxicity (H-HT):	0.146
Drug-inuced Liver Injury (DILI):	0.941
AMES Toxicity:	0.517
Rat Oral Acute Toxicity:	0.011
Maximum Recommended Daily Dose:	0.243
Skin Sensitization:	0.087
Carcinogencity:	0.018
Eye Corrosion:	0.003
Eye Irritation:	0.111
Respiratory Toxicity:	0.583

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC474360

Natural Product ID:	NPC474360
*Common Name:**	2-Hydroxygarvin A
IUPAC Name:	methyl 7,9-dihydroxy-3-methoxy-5,5,7-trimethyl-6,8-dioxo-1-propylanthracene-2-carboxylate
Synonyms:
Standard InCHIKey:	PRAZMVBMBFPZFN-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C23H26O7/c1-7-8-12-15-11(10-14(29-5)16(12)20(26)30-6)9-13-17(18(15)24)19(25)23(4,28)21(27)22(13,2)3/h9-10,24,28H,7-8H2,1-6H3
SMILES:	CCCc1c(C(=O)OC)c(OC)cc2c1c(O)c1c(c2)C(C)(C)C(=O)C(C1=O)(C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL465623
PubChem CID:	21609882
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000018] Anthracenes [CHEMONTID:0001911] Anthracenecarboxylic acids and derivatives [CHEMONTID:0002424] Anthracenecarboxylic acids

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO2240	Garveia annulata	Species	Bougainvilliidae	Eukaryota	n.a.	Northeastern Pacific	n.a.	PMID[17067170]
NPO2240	Garveia annulata	Species	Bougainvilliidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
Ki	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1078	Individual Protein	Indoleamine 2,3-dioxygenase	Homo sapiens	Ki	=	2300.0	nM	PMID[545492]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC474360 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	375
0.1-0.2	1665
0.2-0.3	3454
0.3-0.4	8202
0.4-0.5	10335
0.5-0.6	4156
0.6-0.7	6298
0.7-0.8	6744
0.8-0.85	1313
0.85-0.9	146
0.9-0.95	8
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9073	High Similarity	NPC34802
0.906	High Similarity	NPC163948
0.9	High Similarity	NPC260152
0.8954	High Similarity	NPC329933
0.8917	High Similarity	NPC263483
0.8903	High Similarity	NPC217447
0.8896	High Similarity	NPC473113
0.8882	High Similarity	NPC225173
0.8882	High Similarity	NPC163846
0.8859	High Similarity	NPC168471
0.8839	High Similarity	NPC474417
0.8839	High Similarity	NPC149526
0.8824	High Similarity	NPC125801
0.8808	High Similarity	NPC84266
0.8782	High Similarity	NPC175978
0.8766	High Similarity	NPC2569
0.8766	High Similarity	NPC172329
0.8742	High Similarity	NPC94076
0.8742	High Similarity	NPC201297
0.8742	High Similarity	NPC182255
0.8734	High Similarity	NPC4547
0.8734	High Similarity	NPC146211
0.8726	High Similarity	NPC329844
0.8726	High Similarity	NPC477691
0.8718	High Similarity	NPC133856
0.8718	High Similarity	NPC478148
0.8712	High Similarity	NPC473094
0.871	High Similarity	NPC97029
0.871	High Similarity	NPC158338
0.871	High Similarity	NPC65589
0.871	High Similarity	NPC97028
0.871	High Similarity	NPC100985
0.871	High Similarity	NPC291049
0.871	High Similarity	NPC233267
0.871	High Similarity	NPC288036
0.8701	High Similarity	NPC190648
0.8701	High Similarity	NPC56433
0.8701	High Similarity	NPC126767
0.8701	High Similarity	NPC312929
0.8701	High Similarity	NPC245584
0.8701	High Similarity	NPC289042
0.8701	High Similarity	NPC118027
0.8684	High Similarity	NPC66593
0.8679	High Similarity	NPC67197
0.8671	High Similarity	NPC471456
0.8662	High Similarity	NPC477690
0.8662	High Similarity	NPC273483
0.8659	High Similarity	NPC473095
0.8659	High Similarity	NPC473096
0.8654	High Similarity	NPC205766
0.8654	High Similarity	NPC119929
0.8654	High Similarity	NPC294646
0.8654	High Similarity	NPC147735
0.8654	High Similarity	NPC470568
0.8645	High Similarity	NPC105415
0.8645	High Similarity	NPC27221
0.8645	High Similarity	NPC256672
0.8645	High Similarity	NPC7025
0.8634	High Similarity	NPC219686
0.8625	High Similarity	NPC228654
0.8618	High Similarity	NPC250755
0.8609	High Similarity	NPC165172
0.8608	High Similarity	NPC208806
0.8608	High Similarity	NPC210942
0.8608	High Similarity	NPC169990
0.8599	High Similarity	NPC232645
0.8599	High Similarity	NPC72958
0.8599	High Similarity	NPC470569
0.859	High Similarity	NPC198927
0.8581	High Similarity	NPC123202
0.8581	High Similarity	NPC7943
0.8581	High Similarity	NPC22005
0.8571	High Similarity	NPC478019
0.8571	High Similarity	NPC284495
0.8571	High Similarity	NPC243701
0.8562	High Similarity	NPC272196
0.8562	High Similarity	NPC474637
0.8562	High Similarity	NPC201127
0.8553	High Similarity	NPC149618
0.8553	High Similarity	NPC89625
0.8553	High Similarity	NPC226656
0.8553	High Similarity	NPC66508
0.8553	High Similarity	NPC3898
0.8553	High Similarity	NPC66029
0.8544	High Similarity	NPC87708
0.8544	High Similarity	NPC40356
0.8544	High Similarity	NPC154683
0.8537	High Similarity	NPC30027
0.8535	High Similarity	NPC150928
0.8535	High Similarity	NPC255641
0.8535	High Similarity	NPC60413
0.8535	High Similarity	NPC325983
0.8535	High Similarity	NPC290954
0.8535	High Similarity	NPC158866
0.8533	High Similarity	NPC470722
0.8533	High Similarity	NPC156888
0.8533	High Similarity	NPC470721
0.8533	High Similarity	NPC6100
0.8526	High Similarity	NPC37139
0.8526	High Similarity	NPC472841
0.8516	High Similarity	NPC25844
0.8516	High Similarity	NPC473927
0.8509	High Similarity	NPC324736
0.8509	High Similarity	NPC474373
0.8509	High Similarity	NPC470339
0.8506	High Similarity	NPC471305
0.8506	High Similarity	NPC19896
0.8503	High Similarity	NPC470333
0.8491	Intermediate Similarity	NPC472211
0.8491	Intermediate Similarity	NPC214632
0.8491	Intermediate Similarity	NPC472799
0.8487	Intermediate Similarity	NPC315578
0.8485	Intermediate Similarity	NPC76647
0.8471	Intermediate Similarity	NPC6923
0.8471	Intermediate Similarity	NPC80370
0.8471	Intermediate Similarity	NPC269420
0.8462	Intermediate Similarity	NPC478018
0.8462	Intermediate Similarity	NPC259632
0.8457	Intermediate Similarity	NPC472060
0.8457	Intermediate Similarity	NPC470810
0.8457	Intermediate Similarity	NPC143050
0.8457	Intermediate Similarity	NPC472052
0.8457	Intermediate Similarity	NPC47623
0.8457	Intermediate Similarity	NPC470342
0.8457	Intermediate Similarity	NPC186325
0.8457	Intermediate Similarity	NPC472055
0.8456	Intermediate Similarity	NPC213122
0.8452	Intermediate Similarity	NPC312789
0.8452	Intermediate Similarity	NPC473692
0.8452	Intermediate Similarity	NPC134621
0.8447	Intermediate Similarity	NPC246466
0.8442	Intermediate Similarity	NPC167663
0.8442	Intermediate Similarity	NPC53016
0.8438	Intermediate Similarity	NPC318270
0.8431	Intermediate Similarity	NPC110810
0.8431	Intermediate Similarity	NPC11056
0.8428	Intermediate Similarity	NPC51824
0.8428	Intermediate Similarity	NPC45934
0.8428	Intermediate Similarity	NPC268992
0.8428	Intermediate Similarity	NPC113608
0.8428	Intermediate Similarity	NPC470338
0.8428	Intermediate Similarity	NPC142527
0.8428	Intermediate Similarity	NPC470337
0.8424	Intermediate Similarity	NPC477835
0.8424	Intermediate Similarity	NPC125465
0.8421	Intermediate Similarity	NPC26924
0.8421	Intermediate Similarity	NPC1268
0.8418	Intermediate Similarity	NPC474660
0.8418	Intermediate Similarity	NPC315520
0.8418	Intermediate Similarity	NPC202595
0.8412	Intermediate Similarity	NPC70318
0.8411	Intermediate Similarity	NPC53001
0.8411	Intermediate Similarity	NPC290601
0.8405	Intermediate Similarity	NPC472261
0.8405	Intermediate Similarity	NPC117985
0.8405	Intermediate Similarity	NPC189552
0.8405	Intermediate Similarity	NPC273467
0.8402	Intermediate Similarity	NPC295914
0.8397	Intermediate Similarity	NPC267509
0.8397	Intermediate Similarity	NPC237208
0.8397	Intermediate Similarity	NPC300540
0.8397	Intermediate Similarity	NPC211565
0.8397	Intermediate Similarity	NPC124729
0.8397	Intermediate Similarity	NPC60389
0.8395	Intermediate Similarity	NPC477692
0.8395	Intermediate Similarity	NPC177650
0.8393	Intermediate Similarity	NPC229051
0.8393	Intermediate Similarity	NPC131862
0.8393	Intermediate Similarity	NPC472054
0.8387	Intermediate Similarity	NPC95123
0.8387	Intermediate Similarity	NPC66404
0.8387	Intermediate Similarity	NPC189650
0.8385	Intermediate Similarity	NPC180924
0.8377	Intermediate Similarity	NPC232021
0.8377	Intermediate Similarity	NPC40118
0.8377	Intermediate Similarity	NPC49108
0.8377	Intermediate Similarity	NPC126534
0.8375	Intermediate Similarity	NPC93552
0.8375	Intermediate Similarity	NPC107109
0.8375	Intermediate Similarity	NPC192189
0.8375	Intermediate Similarity	NPC193200
0.8366	Intermediate Similarity	NPC472366
0.8365	Intermediate Similarity	NPC305965
0.8365	Intermediate Similarity	NPC230848
0.8365	Intermediate Similarity	NPC258249
0.8364	Intermediate Similarity	NPC316262
0.8364	Intermediate Similarity	NPC314653
0.8355	Intermediate Similarity	NPC87723
0.8355	Intermediate Similarity	NPC4214
0.8355	Intermediate Similarity	NPC475104
0.8354	Intermediate Similarity	NPC10027
0.8354	Intermediate Similarity	NPC65775
0.8354	Intermediate Similarity	NPC4423
0.8354	Intermediate Similarity	NPC144843
0.8354	Intermediate Similarity	NPC84142
0.8354	Intermediate Similarity	NPC77325
0.8354	Intermediate Similarity	NPC473022
0.8354	Intermediate Similarity	NPC473978
0.8354	Intermediate Similarity	NPC315772
0.8353	Intermediate Similarity	NPC470334

Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC474360 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	344
0.1-0.2	1012
0.2-0.3	1592
0.3-0.4	2580
0.4-0.5	1999
0.5-0.6	1046
0.6-0.7	398
0.7-0.8	162
0.8-0.85	17
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.858	High Similarity	NPD6232	Discontinued
0.8537	High Similarity	NPD7473	Discontinued
0.8471	Intermediate Similarity	NPD3226	Approved
0.8333	Intermediate Similarity	NPD2532	Approved
0.8333	Intermediate Similarity	NPD2533	Approved
0.8333	Intermediate Similarity	NPD2534	Approved
0.8333	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8293	Intermediate Similarity	NPD6959	Discontinued
0.8289	Intermediate Similarity	NPD2935	Discontinued
0.8261	Intermediate Similarity	NPD7819	Suspended
0.8182	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8137	Intermediate Similarity	NPD7411	Suspended
0.8129	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8077	Intermediate Similarity	NPD7003	Approved
0.8075	Intermediate Similarity	NPD6599	Discontinued
0.8052	Intermediate Similarity	NPD5406	Approved
0.8052	Intermediate Similarity	NPD5405	Approved
0.8052	Intermediate Similarity	NPD5404	Approved
0.8052	Intermediate Similarity	NPD5408	Approved
0.8038	Intermediate Similarity	NPD7390	Discontinued
0.8036	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD2346	Discontinued
0.8	Intermediate Similarity	NPD7075	Discontinued
0.7988	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7974	Intermediate Similarity	NPD1607	Approved
0.7966	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7927	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7927	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD5844	Phase 1
0.7892	Intermediate Similarity	NPD3749	Approved
0.7875	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7871	Intermediate Similarity	NPD1510	Phase 2
0.7843	Intermediate Similarity	NPD1240	Approved
0.7831	Intermediate Similarity	NPD7768	Phase 2
0.7791	Intermediate Similarity	NPD7458	Discontinued
0.7785	Intermediate Similarity	NPD2800	Approved
0.7771	Intermediate Similarity	NPD3817	Phase 2
0.7764	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7758	Intermediate Similarity	NPD6801	Discontinued
0.7744	Intermediate Similarity	NPD4380	Phase 2
0.7742	Intermediate Similarity	NPD6651	Approved
0.7736	Intermediate Similarity	NPD3750	Approved
0.7736	Intermediate Similarity	NPD4628	Phase 3
0.7736	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7716	Intermediate Similarity	NPD1512	Approved
0.7707	Intermediate Similarity	NPD6100	Approved
0.7707	Intermediate Similarity	NPD6099	Approved
0.7706	Intermediate Similarity	NPD5711	Approved
0.7706	Intermediate Similarity	NPD5710	Approved
0.7702	Intermediate Similarity	NPD6799	Approved
0.7683	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD1283	Approved
0.7658	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7658	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD1934	Approved
0.7643	Intermediate Similarity	NPD2799	Discontinued
0.764	Intermediate Similarity	NPD8150	Discontinued
0.7616	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD6166	Phase 2
0.761	Intermediate Similarity	NPD1549	Phase 2
0.7605	Intermediate Similarity	NPD2801	Approved
0.7593	Intermediate Similarity	NPD1511	Approved
0.7584	Intermediate Similarity	NPD1201	Approved
0.7557	Intermediate Similarity	NPD6559	Discontinued
0.754	Intermediate Similarity	NPD7435	Discontinued
0.7533	Intermediate Similarity	NPD3972	Approved
0.7515	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD3882	Suspended
0.75	Intermediate Similarity	NPD1470	Approved
0.7486	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD2796	Approved
0.7484	Intermediate Similarity	NPD2313	Discontinued
0.7484	Intermediate Similarity	NPD1551	Phase 2
0.7484	Intermediate Similarity	NPD3764	Approved
0.7484	Intermediate Similarity	NPD3268	Approved
0.7473	Intermediate Similarity	NPD6782	Approved
0.7473	Intermediate Similarity	NPD6778	Approved
0.7473	Intermediate Similarity	NPD6781	Approved
0.7473	Intermediate Similarity	NPD6779	Approved
0.7473	Intermediate Similarity	NPD6780	Approved
0.7473	Intermediate Similarity	NPD6777	Approved
0.7473	Intermediate Similarity	NPD6776	Approved
0.7472	Intermediate Similarity	NPD8313	Approved
0.7472	Intermediate Similarity	NPD8312	Approved
0.7467	Intermediate Similarity	NPD1281	Approved
0.7453	Intermediate Similarity	NPD1243	Approved
0.745	Intermediate Similarity	NPD4626	Approved
0.7444	Intermediate Similarity	NPD8434	Phase 2
0.7439	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD1471	Phase 3
0.7438	Intermediate Similarity	NPD2344	Approved
0.7429	Intermediate Similarity	NPD7177	Discontinued
0.7421	Intermediate Similarity	NPD3748	Approved
0.7396	Intermediate Similarity	NPD1465	Phase 2
0.7394	Intermediate Similarity	NPD6273	Approved
0.7389	Intermediate Similarity	NPD2979	Phase 3
0.7383	Intermediate Similarity	NPD1651	Approved
0.7368	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7354	Intermediate Similarity	NPD7698	Approved
0.7354	Intermediate Similarity	NPD7696	Phase 3
0.7354	Intermediate Similarity	NPD7697	Approved
0.7353	Intermediate Similarity	NPD5402	Approved
0.7349	Intermediate Similarity	NPD920	Approved
0.7338	Intermediate Similarity	NPD2798	Approved
0.7337	Intermediate Similarity	NPD37	Approved
0.733	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD919	Approved
0.7318	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7316	Intermediate Similarity	NPD7871	Phase 2
0.7316	Intermediate Similarity	NPD7870	Phase 2
0.7312	Intermediate Similarity	NPD4308	Phase 3
0.7308	Intermediate Similarity	NPD4625	Phase 3
0.7306	Intermediate Similarity	NPD7874	Approved
0.7306	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD6797	Phase 2
0.7303	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD7229	Phase 3
0.7293	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD5494	Approved
0.7278	Intermediate Similarity	NPD4060	Phase 1
0.7273	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD1164	Approved
0.7273	Intermediate Similarity	NPD1203	Approved
0.7263	Intermediate Similarity	NPD7251	Discontinued
0.7261	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD2309	Approved
0.7254	Intermediate Similarity	NPD8151	Discontinued
0.7247	Intermediate Similarity	NPD7074	Phase 3
0.7246	Intermediate Similarity	NPD5403	Approved
0.7246	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD1247	Approved
0.7232	Intermediate Similarity	NPD3751	Discontinued
0.7232	Intermediate Similarity	NPD3818	Discontinued
0.7229	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD6234	Discontinued
0.7222	Intermediate Similarity	NPD7808	Phase 3
0.7212	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD4967	Phase 2
0.7209	Intermediate Similarity	NPD4965	Approved
0.7209	Intermediate Similarity	NPD4966	Approved
0.7207	Intermediate Similarity	NPD5953	Discontinued
0.7205	Intermediate Similarity	NPD7033	Discontinued
0.7205	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD6534	Approved
0.7204	Intermediate Similarity	NPD6535	Approved
0.7202	Intermediate Similarity	NPD7701	Phase 2
0.72	Intermediate Similarity	NPD3787	Discontinued
0.7197	Intermediate Similarity	NPD7095	Approved
0.7191	Intermediate Similarity	NPD7054	Approved
0.7191	Intermediate Similarity	NPD7286	Phase 2
0.719	Intermediate Similarity	NPD1608	Approved
0.7179	Intermediate Similarity	NPD7783	Phase 2
0.7179	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD3266	Approved
0.7161	Intermediate Similarity	NPD3267	Approved
0.7161	Intermediate Similarity	NPD2797	Approved
0.716	Intermediate Similarity	NPD2438	Suspended
0.7159	Intermediate Similarity	NPD3926	Phase 2
0.7152	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD5691	Approved
0.7152	Intermediate Similarity	NPD411	Approved
0.7151	Intermediate Similarity	NPD7472	Approved
0.7135	Intermediate Similarity	NPD8320	Phase 1
0.7135	Intermediate Similarity	NPD8319	Approved
0.7134	Intermediate Similarity	NPD6832	Phase 2
0.7126	Intermediate Similarity	NPD5401	Approved
0.7125	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD3300	Phase 2
0.7107	Intermediate Similarity	NPD8032	Phase 2
0.7099	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD5760	Phase 2
0.7093	Intermediate Similarity	NPD5761	Phase 2
0.7092	Intermediate Similarity	NPD7801	Approved
0.709	Intermediate Similarity	NPD7700	Phase 2
0.709	Intermediate Similarity	NPD7699	Phase 2
0.7078	Intermediate Similarity	NPD9717	Approved
0.7067	Intermediate Similarity	NPD9493	Approved
0.7063	Intermediate Similarity	NPD4307	Phase 2
0.7063	Intermediate Similarity	NPD943	Approved
0.7062	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD2531	Phase 2
0.7053	Intermediate Similarity	NPD8285	Discontinued
0.7048	Intermediate Similarity	NPD6190	Approved
0.7044	Intermediate Similarity	NPD6798	Discontinued
0.7033	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD6823	Phase 2
0.7019	Intermediate Similarity	NPD230	Phase 1
0.7019	Intermediate Similarity	NPD447	Suspended
0.7012	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD7236	Approved
0.6993	Remote Similarity	NPD1778	Approved
0.6993	Remote Similarity	NPD3019	Approved
0.6993	Remote Similarity	NPD17	Approved
0.6989	Remote Similarity	NPD4287	Approved
0.6988	Remote Similarity	NPD8166	Discontinued

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data